Mechanistic pathways of aromatic nucleophilic substitution in conventional solvents and ionic liquids

被引：42

作者：

Gazitua, Marcela ^{[1
]}

Tapia, Ricardo A. ^{[2
]}

Contreras, Renato ^{[3
]}

Campodonico, Paola R. ^{[1
]}

机构：

[1] Clin Alemana Univ Desarrollo, Fac Med, Ctr Quim Med, Santiago 7710162, Chile

[2] Pontificia Univ Catolica Chile, Fac Quim, Santiago 7820436, Chile

[3] Univ Chile, Fac Ciencias, Dept Quim, Santiago, Chile

来源：

NEW JOURNAL OF CHEMISTRY | 2014年 / 38卷 / 06期

关键词：

SECONDARY-AMINES; ARYL AZIDES; SOLVATION; BENZENESULFONATES; REGIOSELECTIVITY; KINETICS; 1-FLUORO-2,4-DINITROBENZENE; RATIONALIZATION; AMINOLYSIS;

D O I：

10.1039/c4nj00130c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Solvation effects on the reaction mechanism of the title reactions have been kinetically evaluated in 21 conventional solvents and 17 ionic liquids. Solvent polarity affects the catalyzed and non-catalyzed SNAr pathways differently. The ambiphilic character of water and formamide, which act as a hydrogen bond donor/acceptor, induces nucleophilic activation at the nitrogen center of the nucleophile. The ionic liquid EMIMDCN appears to be the best solvent for the SNAr route probably due to the high polarizability of the dicyanamide anion.

引用

页码：2611 / 2618

页数：8

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